Ammonia → HCID 25212020, compound

HRID 1514138Notes

Reaction equation

HRID 1514138 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C:14]2[S:15][C:16]([C:19]3[C:23]([CH3:24])=[C:22]([C:25]([F:28])([F:27])[F:26])[O:21][N:20]=3)=[CH:17][CH:18]=2)=[O:13])[CH2:7]1)=O)C.[NH3:29]>>[CH3:24][C:23]1[C:19]([C:16]2[S:15][C:14]([C:12]([N:8]3[CH2:9][CH2:10][CH2:11][C@H:6]([C:4]([NH2:29])=[O:3])[CH2:7]3)=[O:13])=[CH:18][CH:17]=2)=[N:20][O:21][C:22]=1[C:25]([F:27])([F:28])[F:26]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 25211913HCID 25211913, compound

Product 1

HCID 25212020HCID 25212020, compoundYield 86%

Procedure

A solution of (S)-1-[5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl) -thiophene-2-carbonyl]-piperidine-3-carboxylic acid ethyl ester (Example 65, 88 mg, 0.20 mmol) in 7N methanolic ammonia (5 mL) was heated at 60° C. in a sealed vial for 48 hr. After this time the reaction mixture was evaporated and triturated and filtered with the aid of water. The filtered solids were air dried to afford product as a colorless solid (67 mg, 86%). LC/MS 5.52 min, [M+1]+ 388.

Workup

  1. customAfter this time the reaction mixture was evaporated
  2. customtriturated
  3. filtrationfiltered with the aid of water
  4. customdried

Sources & evidence

ORD record
ord-33302f6c1ddd41f7921b96e63d07ed28
Source dataset
uspto-grants-2012_07
Patent number
US08222243B2

Reaction notes

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